Dichloromethane → HCID 14742798, compound

HRID 1651246Notes

Reaction equation

HRID 1651246 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([O:17][CH3:18])=[CH:7][C:6]=1C=O)[CH2:2][CH2:3][CH3:4].[C:21]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23]C)=[O:22].[OH-].[Na+].Cl[CH2:48]Cl>CO>[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([O:17][CH3:18])=[CH:7][C:6]=1/[CH:48]=[CH:25]/[C:21]([OH:23])=[O:22])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14742769HCID 14742769, compound

Product 1

HCID 14742798HCID 14742798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 111, 1-butyl-4,7-dimethoxy-2-naphthalenecarboxaldehyde (1.35 g) and (carbomethoxymethylene)triphenylphosphorane (1.35 g) in dichloromethane (10 mL) was stirred at room temperature for 42 hours. The crude ester obtained from the usual work up was dissolved in methanol (25 mL) containing 1N sodium hydroxide solution (4 mL) and heated at reflux for 2 hours. The normal isolation procedure furnished 0.725 g of (E)-3-(1-butyl-4,7-dimethoxy-2-naphthalenyl)-2-propenoic acid. A portion was crystallized from diethyl ether-hexane to give the analytical specimen, mp 174°-176° C. Anal. Calcd for C19H22O4 : C, 72.59; H, 7.05 Found: C, 72.58; H, 7.18

Workup

  1. customThe crude ester obtained from the usual work
  2. temperatureheated
  3. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-6bdd8fb6df3043e99a27d57f6fc135bb
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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